Synthesis of novel halo and tosyloxy nortropane derivatives as efficient precursors for the one-step synthesis of the dopamine transporter PET ligand [(18)F]FECNT

J Labelled Comp Radiopharm. 2014 Mar;57(3):148-57. doi: 10.1002/jlcr.3181. Epub 2014 Feb 5.

Abstract

The fluorine-18 labeled nortropane derivative 2β-carbomethoxy-3β-(4-chlorophenyl)-8-(2-fluoroethyl)-nortropane (FECNT) is a dopamine transporter (DAT) ligand. Currently, it is considered as reference for positron emission tomography imaging. Herein, the synthesis of novel precursors (N-tosyloxy-, chloro-, and bromo- analogues) for one-step radiosynthesis of [(18)F]FECNT is reported. Using the N-mesyloxy- precursor in a one-step radiosynthesis, the crude [(18)F]FECNT was obtained with the radiolabeling yield of 45 ± 10%, confirming the practical efficiency of this approach in the design of novel precursors for labeling.

Keywords: [18F]FECNT; one-step; precursors; radiofluorination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic
  • Dopamine Plasma Membrane Transport Proteins / metabolism*
  • Ligands
  • Nortropanes / chemical synthesis*
  • Nortropanes / chemistry
  • Nortropanes / metabolism*
  • Positron-Emission Tomography*
  • Radiochemistry

Substances

  • 2-carbomethoxy-3-(4-chlorophenyl)-8-(2-fluoroethyl)nortropane
  • Dopamine Plasma Membrane Transport Proteins
  • Ligands
  • Nortropanes